US5367078AExpiredUtility

3-oxadiazolyl-1,6-naphthyridine derivatives

67
Assignee: DAINIPPON PHARMACEUTICAL COPriority: Sep 2, 1992Filed: Aug 27, 1993Granted: Nov 22, 1994
Est. expirySep 2, 2012(expired)· nominal 20-yr term from priority
Inventors:Kazunori OhnoOsamu OdaiYukio TominagaKiyoshi FurukawaMakoto Oka
C07D 471/04
67
PatentIndex Score
8
Cited by
25
References
18
Claims

Abstract

3-Oxadiazolyl-5,6,7,8-tetrahydro-1,6-naphthyridine derivative of the formula (I): <IMAGE> (I) wherein Het is an oxadiazole ring, R1 is hydrogen atom, an acyl group, a lower alkyl group or a group of the formula: -CH2R1' (in which R1' is a cyclo-lower alkyl group, a lower alkenyl group, a lower alkynyl group, benzyl group, aryl group or a heteroaromatic groups), R2 is a lower alkyl group, a cyclo-lower alkyl group, a lower alkenyl group, a lower alkynyl group, aryl group, a heteroaromatic group, a halogeno-lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a phenoxy group, or a lower alkylthio group, or a pharmaceutically acceptable acid addition salt thereof, which are useful as benzodiazedine receptor agonist.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A 3-oxadiazolyl-5,6,7,8-tetrahydro-1,6-naphthyridine derivative of the formula (I): ##STR252## wherein Het is an oxadiazole ring, R 1  is hydrogen atom, an acyl group, a lower alkyl group or a group of the formula: --CH 2  R 1  ' (in which R 1  ' is a cyclo-lower alkyl group, a lower alkenyl group, a lower alkynyl group, benzyl group, aryl group or a heteroaromatic group), R 2  is a lower alkyl group, a cyclo-lower alkyl group, a lower alkenyl group, a lower alkynyl group, aryl group, a heteroaromatic group, a halogeno-lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a phenoxy group or a lower alkylthio group, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       2. The compound according to claim 1, wherein R 1  is a group of the formula: --CH 2  R 1  ' (in which R 1  ' is phenyl group, a substituted phenyl group, or a 5-membered heteroaromatic group), R 2  is a lower alkyl group, a cyclo-lower alkyl group, a lower alkenyl group phenyl group or a substituted phenyl group, a 5-membered heteroaromatic group or a lower alkoxy group, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       3. The compound according to claim 2, wherein R 2  is an alkyl group having 1 to 3 carbon atoms, cyclopropyl group, or an alkoxy group having 1 to 3 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       4. The compound according to claim 3, wherein Het is 1,3,4-oxadiazole ring, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       5. The compound according to claim 3, wherein Het is 1,2,4-oxadiazole ring, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       6. The compound according to claim 4, which is 6-benzyl-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       7. The compound according to claim 4, which is 6-(2-chlorobenzyl)-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       8. The compound according to claim 4, which is 6-(4-chlorobenzyl)-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       9. The compound according to claim 4, which is b 6-(2-bromobenzyl)-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       10. The compound according to claim 4, which is 6-(2-chloro-5-fluorobenzyl)-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       11. The compound according to claim 4, which is 6-(2-bromo-5-fluorobenzyl)-3-(5-methoxy-1,3,4-oxadiazol-2-yl)5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       12. The compound according to claim 4, which is 6-benzyl-3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       13. The compound according to claim 4, which is 6-benzyl-3-(5-ethyl-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       14. The compound according to claim 4, which is 6-benzyl-3-(5-isopropyl-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       15. The compound according to claim 5, which is 6-benzyl-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       16. The compound according to claim 5, which is 6-benzyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       17. The compound according to claim 5, which is 6-benzyl-3-(5-ethyl-1,2,4-oxadiazol-3-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       18. The compound according to claim 5, which is 6-benzyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, or a pharmaceutically acceptable acid addition salt thereof.

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